1. Field of the Invention
The present invention relates to a catalytic process for the prduction of a substituted ketone by reacting an organic halide with a ketone in the presence of an alkali metal hydroxide with the elimination of hydrogen halide. More particularly, this invention relates to a process for the production of a substituted ketone which comprises reacting an organic halide with a ketone containing an active hydrogen atom at the .alpha.-position to the carbonyl group in the presence of an aqueous alkali metal hydroxide and a specific nitrogen base catalyst.
2. Description of the Prior Art
The reaction between an organic halide and a ketone containing an active hydrogen atom at the .alpha.-position to the carbonyl group in the presence of an alkali metal hydroxide and a catalyst has heretofore been known. This reaction is represented by the following reaction scheme: ##EQU1## WHERE M is an alkali metal.
Since water is produced in this reaction, it is practically impossible to carry out the reaction under absolutely anhydrous conditions, It has heretofore been generally held that one must strictly avoid adding a considerable amount of water to the reaction system at the beginning of the reaction since the presence of water in the reaction system markedly effects the yield of the product. Therefore, the addition of water with the reactants has been restricted in general, and the alkali metal hydroxide has been added in solid form to the reaction system. For example, it is described in Japanese Patent Publication No. 22,251/1965, which corresponds to U.S. Pat. No. 3,668,255, that the dryness of the reactants is not critical when the reaction is conducted with an amine catalyst but in most cases the reaction proceeds without difficulty even in the presence of not more than 2 moles of water per 1 mole of the organic halide. However, all of the reactions described in said patents are effected substantially under anhydrous conditions.
The present inventors illustratively effected the following experiment. When prenyl chloride was reacted with acetone in the presence of an alkali metal hydroxide, the very small amount of water contained in the acetone inhibited the progress of the reaction, and an amount of water contained in such reactants as potassium iodide, sodium iodide, dimethyl sulfone, sulfolane, tributylphosphine, tributylphosphine oxide, methylamine, dimethylamine, trimethylamine, ethylamine, cyclohexylamine, or ammonium chloride noticeably lowered the yield. Even from the point of view of the economic effects derived from the abridgement of the need for strictly drying the reactants, the allowable water content was only 2.0 moles per 1 mole of the organic halide.